“[Cuban’s] lesson for startups was, ‘You can’t hedge your bets.’ You just have too few resources. There’s too little time. The incumbents are too big, that you have no ability — you cannot go sort of down two parallel paths, get defocused. You have to stay incredibly focused. And, in general, it’s a principle we lived by for a very long time.”

At the time, Box wasn’t sure if it should be consumer-focused, like Dropbox, or an enterprise app targeting larger businesses. Levie says after hearing Cuban’s advice, the company made the decision to go all-in in the enterprise segment and the rest is history.

“To this day, we are incredibly glad that we made that decision of not hedging our bets. We focused on one market, and that is, I think, your only ability to survive and succeed as a startup,” Levie said.

This isn’t the first time Levie shared this story about Cuban. But he says he likes retelling this story because it’s had such a profound impact on the company in its early days.

“I do like to kind of retell [it], because it was meaningful when it was given and I still generally live by it today,” he said.